1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

HRID 251205

Reaktionsgleichung

Reaktionsgleichung von HRID 251205
[CH3:1][C:2]1[C:3]([CH:8]([NH2:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][CH2:24][CH:25]=O.[BH-](O[C:37]([CH3:39])=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[C:3]([CH:8]([N:10]([CH:39]2[C:37]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:3][CH2:8][CH2:9]2)[CH2:25][CH2:24][CH2:23][CH2:22][N:13]2[C:14](=[O:21])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]2=[O:11])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 457911661-(3-Methylpyridin-2-yl)ethan-1-amine

Produkt 1

HCID 672725222-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of the above amine and 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (127 mg, 0.58 mmol) in CH2Cl2 (2.5 mL) was added NaBH(OAc)3 (117 mg, 0.55 mmol) and the reaction was stirred at room temperature under N2 for 16 hours. The mixture was diluted with saturated aqueous NaHCO3 (10 mL) and was extracted with CH2Cl2 (10 mL×3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1) gave 2-{4-[[1-(3-methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a 1:1 mixture of two diastereomers (72 mg, 0.15 mmol, 43%) along with some single diastereomer (33 mg, 0.07 mmol, 20%).

Aufarbeitung

  1. extractionwas extracted with CH2Cl2 (10 mL×3)
  2. dry with materialThe combined organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0f15f6ef15d4b0cb2055b86bf23ad42
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863293B2

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